Jump to main content
Jump to site search
PLANNED MAINTENANCE Close the message box

Scheduled maintenance work on Wednesday 22nd May 2019 from 11:00 AM to 1:00 PM (GMT).

During this time our website performance may be temporarily affected. We apologise for any inconvenience this might cause and thank you for your patience.


Issue 14, 2013
Previous Article Next Article

Synthetic and mechanistic insight into nosylation of glycine residues

Author affiliations

Abstract

The Fukuyama–Mitsunobu alkylation procedure is widely used to introduce alkyl substituents to amino groups in general and N-alkylation of peptides in particular. Here we have investigated the procedure in detail for N-alkylation of peptides with N-terminal glycine residues, based on the observation that standard conditions lead to substantial bis-nosylation of the glycine amino group. A systematic evaluation of this observation was carried out and it was demonstrated that for peptides with alanine, β-alanine or γ-aminobutyric acid (GABA) as N-terminal residues mono-nosylation was observed under the same conditions. Moreover, bis-nosylation was independent of the type of resin, neighboring amino acid and nature of the peptide. Calculations suggest that the reason for the bis-nosylation is the fact that the deprotonated mono-nosyl species is particularly stable in the case of the terminal Gly residue because the N residue can become closer to the SO2 unit. Finally, the mono-nosylated N-terminal glycine could be obtained by careful optimization of the procedure, adding only one equivalent of 2-nitrobenzenesulfonyl chloride.

Graphical abstract: Synthetic and mechanistic insight into nosylation of glycine residues

Back to tab navigation

Supplementary files

Publication details

The article was received on 30 Jul 2012, accepted on 30 Jan 2013 and first published on 19 Feb 2013


Article type: Paper
DOI: 10.1039/C3OB00014A
Org. Biomol. Chem., 2013,11, 2288-2293

  •   Request permissions

    Synthetic and mechanistic insight into nosylation of glycine residues

    N. Stuhr-Hansen, T. I. Sølling and K. Strømgaard, Org. Biomol. Chem., 2013, 11, 2288
    DOI: 10.1039/C3OB00014A

Search articles by author

Spotlight

Advertisements